Methylamine → 1-[5-Fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]-N-methylmethanamine

HRID 38911Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH:13]2[O:18][C:17]3[CH:19]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=[C:22]([F:23])[C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH3:28][NH2:29]>C(#N)C>[F:23][C:22]1[C:16]2[O:15][CH2:14][CH:13]([CH2:12][NH:29][CH3:28])[O:18][C:17]=2[CH:19]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of [5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.4 g, 1 mmol), methanamine (1 ml, 40% in water) and ACN (3 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on flash column chromatography (EtOAc/MeOH) gave the title compound. Yield: 0.2 g, 69%. The amine was converted to the hydrochloric acid salt and crystallized from EtOH/Et2O. M.p. 243° C. MS m/z (rel. intensity, 70 eV) 275 (M+, 81), 97 (48), 70 (bp), 69 (73), 63 (58).

Workup

customPurification on flash column chromatography (EtOAc/MeOH)

Sources & evidence

ORD record: ord-109563af41044050b46ecc30841e6c23
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524766B2

Reaction notes

Loading…